Growing up in Northern Ontario is not exactly the normal childhood. One is excluded from many of the pleasures of city life. The shopping is limited, you end up seeing the hit movies about a year after everyone else has gotten bored of them and none of the adults seem to care what you do with yourself, so long as you keep busy and out of trouble.
My childhood in this environment was particularily strange - I lived with my two sisters and my single mother (My father died in a traffic accident when I was three years old). Being the only boy in the household, I was constantly subjected and drawn into girly games like house or playing with barbies. Not that I minded - After all, even these could provide some entertainment.
My mother was the head of a small technology company based in Toronto. Resultingly, she often left on business trips leaving us kids at home for several days at a time with a babysitter. When my oldest sister, Sarah, turned 14 (I was 11 years old, and Angie was 9 at the time) the babysitter was deemed to be no longer necessary as our mother felt that Sarah was responsible enough to make sure everything was alright.
One Friday night, Angie and I found ourselves at a loose end. Our mother was off until Monday on another business trip, leaving us at home to keep ourselves amused. It was January and the chill winds and blowing snow made any outdoor activity quite unpleasant. Sarah had invited her friend best friend Kate over. With Kate and Sarah occupied chatting in my sister's room this left only Angie and I sitting in the livingroom, staring blankly at the TV. Angie was obviously growing bored. She would fidget every few minutes, toying with her hair, changing her sitting position on the couch or just annoyingly poking me for her own amusement.
After a while I sighed, shutting off the TV and glancing over at Angie. She smiled innocently, her hand half-extended, about to prod me in the side again. She was getting really annoying, and I decided that I should probably keep her occupied until her bedtime, or else she would drive me mad.
"Angie." I said, pushing her hand away from me irritably. "Want to play a game before bed?"
She giggled and nodded eagerly, then asked, "House?"
I groaned. House. I hated house. Usually it involved almost no action, sitting around in a make-beleive kitchen cooking, watching Angie pretend to cry. Still, I suppose it was a better option then boredly sitting there getting repeatedly poked by my little sister.
I reluctantly agreed to play. Angie immediately scampered off to Sarah's room, and after a bit of whining and crying, managed to persuade Sarah and Kate to join in. Angie always got her way. Mom seemed to favor her, and if Angie complained when mom came home it was always hell for Sarah and I.
We all walked into Angie's room - it was our usual playplace for house. There were the necessary plastic dishes for the kitchen, as well as a bed and a fake plastic oven.
Angie was quick to dish out roles for us, eager to start the game. Sarah was the mother, Kate the father (Naturally, the oldest two among us got the parental roles), I was the older brother, and Angie my little sister. Kate, not familiar with the fact that Angie always got her way, complained that there should be two daughters as boys were 'icky'. Angie didn't really seem to care - surprisingly - but I was reluctant to play the role of a girl. Not that it made a difference, it was just a stupid game anyway. I started to argue that I should be the dad then, and Kate the mother, but found myself quickly silenced by Angie's annoying whining - who just wanted to start. I sighed softly to myself, accepting my role as a girl, and we started into the game.
As usual, it was boring. The mom and dad would stand around the kitchen cooking, us kids would sit on the floor playing with toys, Angie occasionally whining for attention from her 'parents'. Both I, Sarah and Kate were unenthusiastic, and I think the only thing that kept me from standing up and walking out were the occasional smiles that Kate would cast me. I had a crush on her.
As it neared 8:00 - Angie's bedtime - there came an argument. I was supposed to be their daughter, yet my clothes were clearly male. Baggy jeans and a white tee-shirt. Kate, a bit of a tomboy was clad nearly the same as me only her jeans were a bit tigher. Her clothing passed as either male or female I suppose. Angie, being her impatient self, whined. She didn't suggest any solution - probably not having one - just hoping that somehow making herself sound irritated would help the problem. Sarah, Kate and I all glanced back and forth from one another hopelessly, as if each was expecting the other two to come up with a solution to the irritating whines.
Kate was the first to speak, "Matt, " she said, facing me, "why don't you go put on some of Angie's clothes? She's about your size."
Needless to say, I blushed a bright red. To play the role of a girl was one thing, but to dress up as one quite another. I opened my mouth starting to object, but was quickly silenced by a hard look from Sarah as Angie's crying grew louder again. I ambled slowly over to Angie's walk-in closet and stepped in, shutting the door behind me. I slipped off my clothes quickly, piling them on the floor, then glanced around and found a pair of little pink panties. I looked down at them scowling. It should have been easy - all that I had to do wasstep into them - but to actually think about doing it brought the blush back to my face.
I stood there unmoving for several minutes, just holding the panties. By the noise outside, it sounded as if the game had resumed. A knock on the door disturbed the silence, "How's it coming Matt?" came Kate's voice through the door.
"Uhm, I can't figure out how to get this stuff on." I said, "I guess I'll have to just stay in my regular clothes...". I put the panties back down, picking up my navy blue boxers.
"Oh nonsense, here I'll help you." Came Kate's voice.
The door swung open, and Kate, not even taking a second glance at my naked body, stepped in, closing the door behind her. I turned my head over my shoulder, staring at her with a bright pink blush on my face, but she seemed to take no notice.
Kate picked up the panties that I had just dropped moments ago, and leaned down, holding them by my feet. "Ok, just step in hun, like you would for your boxers."
I quickly did as she asked, wanting to hide my nudity and Kate pulled the panties slowly up my legs to cover my crotch. They were pretty tight on me and the silky fabric squeezed in gently around my cock, creating a slight bulge at the front. Kate tugged them up another little bit, creating even more pressure against my cock and I let out a low groan, blushing.
"See, they're not that bad, are they sweetie?" Kate giggled, then smiled, and gave my a light kiss on the cheek, once again drawing a pink blush to my face - A blush that brightened substantially as her hands began to smoothe out the panties accross my skin, brushing against my rear, then against my cock. Her hands were warm and with the stimulation of the smoothe fabric against my cock, I felt myself growing hard. I let out a soft gasp. Kate simply looked at my growing bulge beneath the panties and giggled.
"Enjoying this now, aren't you sweetie?"
She went back to Angie's drawers, finding a little black skirt, a pink bra that matched the panties and a tight-fitting red tee-shirt. First she had me step into the skirt, pulling it up my legs and buttoning it up, concealing the panties and the bulge beneath. Next she held the bra to my chest, and buckled it around. She looked at it for a moment, then grabbed a pair of socks, stuffing one sock under each cup to make it appear as if I had breasts. Finally she asked my to lift my arms and she slipped the tight red shirt down over my head, hiding the fact that there were real breasts, and completing my outfit.
Kate smiled at me, and wordlessly taking my hand, the opened the door, leading me back out to Angie's bedroom. Upon seeing me, Angie looked delighted, seeing that her demands for the game had - as usual - been met. Sarah simply smiled, perhaps holding back a laugh as she looked upon her little brother in her little sister's clothing. I blushed again, but then looked down at Kate's hand still holding mine and felt reassured - and hard, I noted, as the panties seemed to be growing more tight on me by the moment.
The game flowed smoothely from then on, and we played for another ten minutes before it was Angie's bedtime. Rachel, Kate and I waited as Angie got changed into her pyjamas. The whole time, Sarah and Kate were talking excitedly between themselves in whispers, occasionally glancing at me and giggling. Finally, Angie slid under the covers and a walked towards her closet, intending to get back into my clothes. Sarah walked out of the room at a quick whisper from Kate, leaving only Kate, Angie and myself.
As I reached the closet, Kate put grabbed lightly ahold of my wrist, stopping me. She smiled, and casting a quick glance to Angie to make sure she had closed her eyes, Kate's hand darted beneath the skirt, lightly squeezing my cock through my panties. I groaned, blushing and looking back at Kate.
She leaned her head in close to my ear and whispered quietly to me, "Meet me in Sarah's room at midnight. Keep the clothes on."
Her hand brushed softly off of my pantied cock, and she stepped away, walking out of Angie's room. I stood stunned for a moment, opened the closet to collect my clothing I had taken off earlier, then raced back to my room, my heart pounding.
I locked my door behind me, and lay down on my bed panting. She had touched me. Not even accidentally. She had even invited me to the room where she would be sleeping tonight. My mind reeled with possibilities and my hand slid down beneath the panties, stroking myself as I thought.
I imagined Kate on top of me, holding me down on the bed as she rode my cock. She was breathing hard, looking down at me with eyes filled with lust. Beads of sweat formed on her forehead, she moaned and trembled as an orgasm rippled through her, then collapsed down on top of me, breathing hard.
The illusion broke as I felt my own orgasm commence. I spurted a couple drops of cum onto the red tee-shirt (I had only started producing cum in the past month), but my cock pulsed many times as the orgasm shook me. I found myself lying down, panting as the effects of my orgasm receeded, and shut my eyes, continuing to think about Kate.